I considered resurrecting
this one rather than opening a new topic. But this here is also about enjoying to cry + other media.
I have been doing it since I was a kid. I'd love crying at some touching moment of a musical work, a book, a movie or another medium.
With music, I'd just think of a matching place or event and there go tears. As a composer I do cry a lot when writing works that cover matching topics.
Speaking of movies, I roll back particular part of a movie over and over just to boost the effect.

No shame. Then I look myself in the mirror and cry stronger. Cry junkie!
Otherwise, I also have thoughts of original sceneries in public /a no-time-for-that storywriter here/. And those sceneries can be so touching I just start and keep crying. Although I enjoy it, in public it already gets embarrassing. I need my space to cry.
How about you?